Devilish Dates
by The dragon1010
Summary: Oneshot challenge between RedHawkdude, vala411, and I. Hiccup sold his soul to a demon the year before, today the devil gave it back to him asking for a favor. Rules: 6000 word limit and the Devil needs dating advice.


Prompt: I sold my soul to the devil a year ago. He gave it back to me today asking for a favor.

Rules:

6000 word limit, the devil needs dating advice

AN: I had a REALLY fun time writing this story. Made me giggle a bit, made me sad. In the end I hope everyone can get the same experiance out of it, so enjoy.

Exactly one year ago Hiccup Haddock made himself a deal with a demon. You see his mother was a cancer patient and the doctors told him and his father that she had about one year to live. He couldn't accept that fact so he did the unthinkable… he made a deal with a demon, his soul for her life. Once the deal was made he got a call from his father telling him that chemo had worked and the cancer was gone.

He knew in the back of his mind that his parents would be ashamed but he couldn't lose his mother. When he got to the hospital the doctors were doing some final tests but in the end told him that she would live a long life "It looks like you two got a miracle on your hands." The doc said before dismissing us.

Soon after his mother was released did he start to think of the consequences. It scared him, he had no idea what hell would be like. Were the stories true, would he be in misery for eternity? After about a year he stopped thinking about everything hell related and looked at enjoying the life he had. That is until HE showed up.

He got himself an apartment in the city of Berk because he was not going to live in a dorm. Yes, he was in college and not a big fan of being around other people. He had no classes today so he was free to do whatever he wanted.

"Where did I put that damn thing." He muttered looking for his laptop. He pulled off the couch cushions and started to look for them.

"You looking for this?" He let out a yelp before turning around to see a guy with black hair, wearing a hoody, slightly tanned skin, and acidic green eyes holding his laptop.

"W-who are you and what are you doing in here?" He asked glancing over at the door which still had the deadlock closed. The man chuckled for a second "I don't need to use a door."

He gulped "Then who are you?" He set down the computer onto the kitchen table and clasped his hands together "I have many names Satan, Lucifer, but I'm widely known as the devil."

If his eyes could bulge out of his skull, they would have. He thought that he would get a full life but it seems like he wouldn't "Awesome…" He deadpanned.

He sighed and walked over to the fridge to grab an apple "You wanna eat before we go?" He got a funny look from the devil "Where are we going?" He asked.

"Um, are you not here to take my soul?" He asked feeling confused. The devil shook his head "No no, quite the opposite actually. I have a deal for you." He said unclasping his hands.

He stared at him for a couple of seconds "What kind of deal?" The devil put a hand behind his head and started to...blush? He chuckled nervously "Well you see I have and offer that will allow you to keep your soul."

He almost choked on the apple that he took a bite out of "You're serious?" The devil just nodded "Well then, what is this deal?" He asked knowing that it was probably going to be a tough one "Well uh… you see I've been in hell for a long time and I'm a rather lonely person."

He looked at him confused "Sooo what, do you want to spend time with me or something?" He put up his hands and shook his head "Not that kind of lonely, you see I'm looking for… a significant other." He said with his face turning a little red.

His eyes widened a little "So why would you come to me, I'm not exactly a ladies man like, at all." He said feeling confused at why he would choose him for dating, he's never even kissed anyone before. The devil chuckled for a second.

"I know that, but like you, I'm not into women. That's why I chose you." His mouth open wide for a second before shaking his head "I haven't been exactly successful at that either." He mumbled to himself more than the other.

"I know, but you have the right heart which is why I came to you." He said before sitting down at the table. He thought about it for a second "So let me get this straight, you want me to help you find dates?" The devil just nodded back.

He combed his fingers through his hair while nodding "To get my soul back that sounds like a good deal. But if I'm going to do this you can't call yourself Satan or Devil, not very charismatic." He told him "Ok, call me Toothless."

He stared at him for several seconds "Toothless…" He nodded "Yep, that's my actual name not that bible stuff. God's a bit of a joker if you couldn't tell. Plus, your name is Hiccup I think I'm fine." He started at the other boy bluntly "Shut up." He muttered.

Toothless just smirked "So do we have a deal?" He said standing back up up reaching his hand out. He stared at his hand and nodded while grabbing it "We have a deal." He said while shaking Toothless's hand.

He pulled away and Toothless pulled out a piece of paper "This is the contract you made one year ago…" It went up in flames and was in ashes within a second "There, my end of the deal is complete." He said putting the ash off of his hands.

"So I'm just wondering, what is hell actually like?" He asked wondering what he just got out of "Well it's not as bad as mortals portray it, it's just a massive prison that souls are housed for a certain amount of time to be taught a lesson before they are sent back to earth to be reincarnated." He explained.

His eye rose "So… what's the downfall of selling my soul then?" He asked feeling confused at that system "Ahh yes, the people that sold their souls are the work force of hell. They are construction, cooks, and all of the stuff you need to run a society. But they also get let out just a bit later."

That did sound like a pretty sound system "So then wouldn't be being uh… well gay put me in hell anyways?" He asked feeling like he was screwed either way "Not at all, homosexuality isn't a sin at all. Just a myth that got spread around because of me by accident. Some priest died, learned my sexuality and somehow was brought back to life… very long story and I don't want to get into it."

Also good to know "Either way, when do we start?" He asked sounding eager. He brought his hand to his chin and thought for a second before getting an idea "Hand me my laptop." Toothless grabbed it and handed it over.

He opened everything up and got onto an online dating website. Toothless was looking over his shoulder "Does this actually work?" He asked sounding uncertain "I know for a fact it does, my friend Fishlegs found his girlfriend Heather on here." He said clicking create new profile.

"Ok your first and last name."

"Toothless Fury."

"Hight?"

"Six foot."

"Hobbies?"

"Uh… I don't really, have any." He looked at Toothless with a disbelieving look "You are almost as old as time and you don't have a hobby?" He shook his head "Not really, mostly just work." Hiccup thought for a second.

"What are you good at?" Toothless started to think for a second "Well, I do like to cook if that's something?" He nodded and put that in.

"What kind of relationship are you looking for?"

"Long term."

"Job?"

"Uh...manager."

"Where do you live?"

"I was hoping eh… here?" He said sheepishly. He stared at him for several seconds "Fine, but you're sleeping on the couch and paying for your own food. I'm struggling as it is."

He nodded "Sure, I can do that." They went back to the computer and the rest was just basically saying that he wanted a male partner and then the profile picture. Toothless looked a bit shy "What if the picture doesn't looks nice?" He rolled his eyes.

"You look fine trust me." He said with a minor blush forming at his own comment. Toothless leaned up against the wall and crossed his arms. Hiccup raised the camera and took the photo. He looked down at the camera and saw that Toothless had a black fog surrounding him.

He peaked up at him and shrugged "Eh, I can just photoshop it." He said putting the SD card into the computer and doing his magic with photoshop "Aaaand done." He said showing Toothless a picture without the whole hell energy thing "How do I look in it?" He asked.

"As I said you look wonderful." He said putting the picture into the profile section and hitting the submit button "There, we'll check back on it in the morning. Does that sound good?" He asked Toothless who nodded yes.

"Ok then, give me a minute to get your stuff." He said walking into the closet and grabbing blankets and pillows. He tossed them to Toothless "If you need anything else my room is right here, just ask." He said before going into his room to sleep.

The next morning he woke up to an amazing smell "What is that?" He muttered opening his door. Toothless was in the kitchen standing in front of the stove "Morning." He called back to Hiccup. He just yawned and walked over to him rubbing his eyes "What are you making?"

Toothless just shrugged "You didn't have much, but I made sausage and eggs." He was surprised but just let it be "Well, do you want to see if you have anyone that requested a date?" He asked him "We can after breakfast." He said bringing the sausage and eggs to the table.

"Umm, how did you know where the plates were?" Toothless just blushed "I uh, search through all of the cupboards before making food." He chuckled before taking a bite of the sausage "Whoa, this is amazing." He said after swallowing.

Toothless just rubbed the back of his head "It's not that good, I didn't even have all of the ingredients that I needed." He took a couple more bites before speaking again "Well whoever you end up with is lucky to have such an amazing a cook." He said before moving onto the eggs.

"You know Hiccup, it almost sounds like you're hitting on me." He started to choke on eggs and started to sputter "I uh, not trying... you…" Toothless just laughed "I'm messing with you." He said while still laughing. Hiccup just stared at him with a blush apparent on his face "Jerk."

Toothless just continued to smirk all throughout breakfast "You know, I can pay for the food if you continue to cook it." Hiccup said while putting his plate away "Are you making a deal with the devil Hiccup?" He heard the other boy tease.

"Apparently I am, so do you accept?" He said turning back around "I think that can be arranged." Hiccup mentally cheered, no more coffee pot ramen for him. He went over and grabbed his computer before setting it on the table.

"Ok so let's if anyone is interested in dating the devil." He mumbled pulling open the inbox. There were a few "Ok, now you go through all of these and tell me which ones you like and who you will go on a date with first." He said handing the wireless mouse to Toothless "Yes mom."

"Shut up, this was your idea to come to me for dating advice so deal with it." He said before walking over to the sink to clean the dishes. Meanwhile Toothless was going through the messages he had and decided that he like two of the profiles.

"Ok I think these ones will do." Hiccup put the dishes away quickly before taking a seat next to him "Let's see what you've got shall we." He said before reviewing the two profiles. The first one was called… Snotlout…

"Really, Snotlout?" He said looking up "Don't judge, my name is Toothless. It's not much worse." Toothless responded "Speak for yourself." He mumbled to himself before looking at his personality.

He was an athlete that played football, he apparently is a very kind and loving person from his history, and he is willing to go on a date at anytime anywhere. He glanced over at Toothless and opened his mouth before shaking his head and looking at the other profile.

This one is named John "At least one of your options has a normal name." He said trying to tease him "Oh hardy har…" He just rolled his eyes and continued to read into John's profile for his personality.

He was an artist, both musically and with a canvas. Along with that it says that he is a rather calm person that doesn't mind long conversations with people, he would like a calm and collective person like himself. He was willing to go on a date anytime anywhere.

"Not gonna lie, the leaning towards the second one but I'm not you and I don't know the kind of people you like." He said looking over at Toothless "So… who do I go out with first?" He shrugged "No idea, that's your choice."

Toothless sat there for a couple of seconds before shrugging "Well god, I hope you choose well for me." He heard him say before pulling out a old coin "Where the hell did you get that?" Toothless just looked at him blankly "Uh hell, duh. I may have to work there but I still get payed every now and then. Either way, heads for Snotlout and tails for John."

Toothless said before flipping the coin and standing back and letting the coin hit the floor. When it stopped moving both boys leaned over to look at the coin. It landed on heads "Well, the Snot man it is then." Hiccup said before standing up.

Toothless got on the computer and responded saying that he was willing to go on a date. After about five minutes Snotlout asked where they would go and when "Uh Hiccup… what do I do?" He just shrugged "I don't know, think of a place and a time. It's simple." He said before walking into the bathroom with a towel.

Toothless heard the shower start and he looked back at the screen. Where and when would he do this? He thought for several seconds before typing in the chat.

'My place tonight, sound good?' He waited for a couple of seconds before getting a response 'Sure, send me the address so I can find you.' He quickly typed in the address and closed the laptop smiling to himself.

After about fifteen minute Hiccup got out of the shower and walked into his room only to find Toothless in there "TOOTHLESS, what are you doing in my room!?" He shouted. The other boy spun around and looked at him sheepishly "Sorry I uh… I didn't realize that you'd be… I'll leave now." He said before walking out of the room.

Hiccup was standing there supporting a blush that could match the color of a tomato. After several seconds he dropped the towel and quickly threw on clothes. Once he was done with that he went out to ask Toothless why he was in his room.

"Ok, what were you doing?" He said while stepping out of his room "Uh, sorry I thought you would want to know that I kinda made that date here." Toothless said rubbing the back of his head "The date is here…" He said trailing off.

"Ya, tonight." He stared at Toothless for a couple of seconds before groaning and facepalming "Why did you choose my apartment of all places?" He said pulling his hand from his face. Toothless just shrugged "Figured I could put my cooking skills to use here." He said honestly.

"Fine, but if there is a next date… you're going to a restaurant and I don't care if it's McDonalds." He said seriously. Toothless nodded "Ok, ya… sorry for not asking." He just sighed and walked over to grab his laptop.

To be honest the devil had more manners than anyone that he ever dated, or most of the people he's even met. Guess you really can't judge a book by it's cover. He grabbed his computer and textbooks.

"Ok I've got class today so please don't ruin anything in the house… and don't go snooping in my room!" He said before walking over to the door. Before he shut the door he turned around "I won't come home so I don't bug you or your date. But I will be back by 2:00 A.M. Fair enough?"

Toothless nodded and Hiccup shut the door leaving for class. Toothless looked around the apartment "Guess I better clean this up a bit." He muttered to himself before getting to work on cleaning the place up a little.

That Night

Toothless decided that he would make tacos that night along with some chips. He quickly set the plates out when he heard a knock on the door "One second." He called before walking up to the door. He smoothed out his clothes and took a deep breath opening the door.

Standing on the other side was a boy that stood at about 5'10" and had black hair "Hello, come on in." He said welcoming him in. When Snotlout came in he instantly looked at the table "Oh boy, that smells great." He said walking over to the table without acknowledging Toothless.

"Oh boy…" He muttered before walking over to the table and sitting down "My name's Toothless." He said putting his hand out for a handshake "Snotlout…" The other boy said digging right into the tacos not even shaking his hand.

'Great just great.' He thought before grabbing a taco himself and taking a bite "So Snotlout, tell me a bit about yourself." He said wanting to give the boy more of a chance before dismissing him "Mmh, I'm the best football player that Berk had ever seen or will ever see." He said with food in his mouth as he spoke.

Toothless felt this going south faster than a toddler with a gun "Oh that's cool, so you play for the college?" He asked hoping for this to get better "Yep quarterback too." He said with food still in his mouth "Neat, what classes to you all take?"

"Eh, school doesn't matter. It just takes my focus off of what's important and steals my money. I just get passing grades so that I can keep playing." Oh ya this was definitely going to not be good "So why are we at your home, not enough dough to go out?" Yep that was it.

"Excuse me for a minute." He said through gritted teeth "No problem babe, I'll be right here." He got up and walked over to the stove where the meat for the tacos were "Do you want another taco?" Snotlout just nodded rapidly.

He put some meat in the shell before glancing over his shoulder, Snotlout was too busy eating his food to see what he was about to do. He quickly flashed into his own home in hell and went to the fridge to grab something… The Devil's Hot Sauce

He quickly flipped back into the apartment, Snotlout was completely oblivious. He chuckled to himself before pouring a sizeable amount of sauce in each taco "Here you go, enjoy." Snotlout dug in as fast as they touched his plate.

He waited for several seconds for his master concoction to kick in. Snotlout already had one finished and reached for the second one before freezing mid grab "Do you have water these tacos are pretty spicy." He shook his head "I only used mild taco sauce, can you not handle a little spice?"

His taunt worked because Snotlout grabbed the other one and ate it as well. After another minute he could see tears in the boy's eyes "Are you alright?" He said trying to suppress his smile and laugh. He didn't get a reply as Snotlout rand for the sink to drink.

He couldn't help but let a small laugh as Snotlout tried to turn on the water, but her thought ahead and shut the water off. Call it payback or even karma it didn't matter, he was happy that god let him watch this.

He could see the massive amounts of discomfort as Snotlout came back over "So this was nice, call me we should do it again." Snotlout said drooling and crying all at the same time. He quickly handed him his number before walking out of the apartment.

Once the door closed Toothless burst out laughing not able to keep it in anymore. It was his own hot sauce that was twice the heat of a ghost pepper. Along with that it had a natural laxative in it as well so Snotlout will be shitting out pure napalm within twenty four hours.

He kept chuckling but at the same time felt disappointed that it didn't turn out well. It didn't matter though, it gave him a laugh that he needed. As he was putting the dishes away his mind drifted towards Hiccup.

He seemed like a nice enough guy but he was just helping him because he gets to keep his soul. He sighed at his misfortune before cleaning off the table and going to lie down on the couch to sleep.

Next Day

Hiccup found Toothless on the couch the night before but left him be. But now that it was morning he wanted answers so he shook the boy awake "Uhh what do you want?" Toothless mumbled rubbing his eyes.

"Details, did the date go good and is my job done?" He asked. Toothless shook his head "Such a complete asshole that guy was … and that's coming from the devil, I've met plenty of them." Hiccup put his hand onto Toothless shoulder.

"Sorry, that guy did smell a little fishy." Toothless just shook his head "Maybe this whole dating this isn't a good idea, I should just go back to hell." He said standing up "Whoa whoa slow down, it was your first date. Don't let that get you down, you even have one more date that you said you'd go on."

Toothless sighed "I guess that's true." Hiccup nodded "That's the spirit, now tell me what all happened yesterday." He said sitting down on the couch next to Toothless and kicking his feet up ready for the worst date ever.

Toothless told him the entire story almost word for word. By the time Toothless was almost done with the story Hiccup was laughing so hard that his stomach was hurting and along with that he fell half way off of the couch.

"So, how was my first date?" Toothless asked. Hiccup was doing everything in his power to sit up and look him in the eye "It sounds like you have a good story to tell in the future. Man even the twins would like that one." He looked at him funny.

"Twins?" He asked "Don't worry about it… and don't worry about your next date, no doubt in my mind that it will go better." Hiccup said patting him on the back a couple of times "So what do ya say, do you want to go set up another date?" He asked him.

"I guess I can do another one." He said walking with Hiccup over to the computer "Oh but I was serious, no more dates here please." He nodded before pulling up his inbox and accepting John's date request.

After about ten minutes he got a message asking if he was free tonight and if he was willing to go to a nice restaurant on the edge of town. He looked over at Hiccup "I uh… don't own a car." Hiccup rolled his eyes "You can borrow mine, not a looker but it does the job." He said.

Toothless grabbed him in a hug "Oh thank you." He was blushing like a tomato again "N-no p-problem." He stuttered out. When Toothless let go he accepted the offer and Hiccup was looking away trying to get the blush off of his face 'Stupid emotions.'

Toothless air thrusted and turned to him "It's done, John's going to meet me at a place called The Smithy. He said they have good food there." He nodded "Well he's not wrong the cook there is amazing. If you get the chance just tell Gobber that Hiccup sent ya. He'll make you something special… he's my godfather."

He explained at the end seeing Toothless's confusion "Ok cool, thanks." He nodded and grabbed the computer and his textbooks "I have class again today and I won't be back till you are gone so… good luck." Toothless nodded with a smile as he walked out of the door.

That Night

Hiccup took the bus to class and back. He didn't get back until a bit later, Toothless was already gone as he expected him to be. So he clicked on the tv and sat back on the couch. After about thirty minutes he got one hell of a surprise. He heard the door open up and saw a bloody Toothless enter the apartment.

"Toothless what happened!?" He asked feeling extremely worried. Toothless said nothing and walked over to the sink and dipped his head in. Hiccup ran into the bathroom to grab the first aid kit and quickly brought it back to Toothless.

He pulled a chair up and pushed Toothless into it "Ok what the hell happened?" He asked looking at his head to see blood leaking out of the back of his head. Toothless remained silent still "Come on Toothless spill." He said dabbing the blood off of his head.

"I think my time here is up." He heard him say coldly. He froze and went in front of him "Why, please just tell me what happened." He asked feeling genuinely worried "I don't know why I ever thought the devil trying to find love would work anyways." He said pushing Hiccup's hand off and standing up.

Hiccup wasn't having it and grabbed the other boy before shoving him back in the chair "Stay seated I still have to patch up your head and you still have to tell me what happened. No weaseling your way out." He said sternly.

Toothless sighed "Fine, there was no John." He stated. Hiccup just looked at him funny "Please elaborate." He said before cursing to himself after wiping off Toothless's forehead "Looks like you need stitches. I know how but I would advise seeing a doctor." He said noticing the two inch gash on his head.

"You do it, I can at least trust you." He nodded and grabbed the needle and thread "Continue please." He said staring to stitch his head together "Well in the message he told me to meet him in the alleyway next to the restaurant…" Toothless started to fade off.

"What's wrong?" He asked. His eyes widened as he seen a small tear go down Toothless's face "When I went in there there was five teenagers there." He paused and looked him in the eyes "To leave out the details, they beat me up while calling me horrifying names." Toothless said while pulling his knees up to his chest.

He already finished the stitches and felt absolutely disgusted. Once he set the needle down he brought Toothless into a hug "That's terrible." He muttered. Toothless hugged him back while grabbing him tight "I live in hell yes, but souls don't speak or do anything to you but here… people are just evil."

He felt like a dick for asking this question "But I thought you were immortal?" Toothless nodded "All that means is that I can't die, but I can still get hurt." Hiccup squeezed Toothless before letting him go "Well no matter what Toothless I will be there for you, not because of some stupid contract but because I like you."

Toothless smiled and looked into his eyes "So you really mean that?" Hiccup smiled back and nodded "Every word." Both boys stared into each other's eyes and Toothless grabbed the back of Hiccup's head and kissed him for several seconds.

When they both pulled away they stared at each other again. Toothless looked away "I'm sorry I just…" He was cut off as he was pulled into another kiss by Hiccup. After another half a minute they both pulled away trying to catch their breaths

Toothless laughed for a couple of seconds before looking him in the eyes again "I love you Hiccup." He just smiled and pulled Toothless into a hug while giving him a peck on the lips "And I love you too Toothless, ruler of hell." He said with a smile.

Toothless just stood there with a lopsided grin and Hiccup just rolled his eyes "Go take a shower and wash yourself off, you need it." Toothless nodded and grabbed a towel. He watched with a smile as Toothless went into the bathroom and shut the door behind him. He chuckled to himself for a couple of seconds,

"I guess the devil can find love after all."

AN: So ya like I said, had a lot of fun with this one and I will put the propts up on my Bio later today or tomorrow so everyone can know what I will be writting. Also I know Volkin is taking a bit of time but summer break started for me and I became a little lazy. Don't worry though for any Volkin readers I WILL have another chapter up withing the week for sure unless I die or something stupid like that. Either way, I hope this was able to make your day better and I'll see you guys later.

You took the time to read this; you can take the time to review

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